HE WAS a tattoo artist eking out a living in Far East Plaza. She was a lecturer at the Institute of Technical Education who hoped to marry him.
But they had a problem. He was dead broke.
There were some months when he made barely $800 and had to sell his precious watch collection to survive. Within six months, he parted with two Rolex watches, three Tag Heuers, one Cartier and one Omega - all for a fire sale price of $7,400.
SIMPLE LIFE: The Teems may make a lot, but they live with their new baby in a three-room flat.
Finally, he had enough.
In 2006, Mr Jude Teem, 35, traded his T-shirts and bermudas for crisp white shirts and tailored trousers and joined real estate agency PropNex as a realtor. His then-girlfriend, Ms Anthea Yeo, 33, quit teaching to do a master's degree and also help him in the trade.
Mr Teem, an N-level holder, made a list of the watches he hoped to buy back when the money rolled in and stuck it on the ceiling above his bed. Every night, he would gaze at the list to spur himself on.
'I never liked to wear long-sleeved shirts and trousers from young. It looked so weird to my friends,' he said.
But the new wardrobe was necessary as his tattoos, which run down his back and the length of both his arms, could turn people off.
Turning from artist to property agent also changed his attitude for good.
'As a tattoo artist, my clients had to see if my mood was good. As an agent, even if my mood is not good, I could not show it.'
He once persuaded a property owner to hold off selling his condominium until a year later, helping him make $200,000 in the process.
'If he had known that I was a new agent, a former tattoo artist, he would not have believed me,' said MrTeem.
While the couple have had mostly good encounters with clients, dealing with unscrupulous counterparts is another matter altogether.
They have come across agents who lend money to hard-up home owners so that they are beholden and then forced to sell their flat at an unfavourable price.
Then there are agents who under-declare the price of the flat so that only a portion of the sale proceeds is refunded into the seller's Central Provident Fund account. The rest is pocketed as cash - with the agent taking a cut.
This practice is illegal but used by sellers to 'withdraw' money from their retirement savings.
Eyes narrowing, the soft-spoken Mr Teem said: 'This money is the sellers' money. It's their future money. It's just not right (that agents take it).'
Once, Ms Yeo found out that an agent had sold his own property to a client without declaring the conflict of interest. She struggled over whether to tell the client and did so in the end.
But she said: 'Sometimes when we see other agents doing unethical things, we have no heart to report them. It's their livelihood at stake.'
Their own livelihood, meanwhile, is anything but struggling. Mr Teem said without a hint of irony that he has stopped calculating how much commission they make from each sale or tenancy deal.
'For the first few cases, we counted how much we made, like $2,000 or $800. After that, we didn't have time to count. We could close four deals in one day.'
As if on cue, Ms Yeo steps away from the interview to take a call - just one of the many which come within the hour.
The couple have celebrated their success with diamonds for her and Rolex, Cartier and Panerai timepieces for him.
But Mr Teem no longer feels the need to replenish his watch collection.
'When you can't afford it, you want it. Now that you can afford it, you feel that you don't need it.'